Month 2014
N-Methylation of 5-Substituted 1H-Tetrazoles with Dimethyl Carbonate
4-(1-Methyl-1H-tetrazol-5-yl)benzaldehyde (3i). The reaction
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was conducted under argon protection. Light yellow solid; yield
1
14%; mp 128–130°C. H NMR (500 MHz, DMSO-d6) δ 10.13
(s, 1H, –CHO), 8.14 (d, 2H), 8.08 (d, 2H), 4.20 (s, 3H, 1-CH3);
13C NMR (126 MHz, DMSO-d6) δ 192.97, 153.47, 137.71,
130.06, 129.71, 126.64, 35.47; MS (ESI): m/z = 189 (M + H)+.
Anal. Calcd for C9H8N4O: C, 57.44; H, 4.28; N, 29.77; O,
8.50. Found: C, 57.65; H, 4.43; N, 29.49.
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4-(2-Methyl-2H-tetrazol-5-yl)benzaldehyde (4i) [21].
The
reaction was conducted under argon protection. White solid, yield
77%. mp 138–140°C. 1H NMR (500MHz, CDCl3) δ 10.10
(s, 1H, –CHO), 8.34 (d, 2H), 8.03 (d, 2H), 4.45 (s, 3H, 2-CH3).
2-Methyl-5-(4-nitrophenyl)-2H-tetrazole (4j) [22]. Yellowish
1
crystal; yield 82%; mp 168–170°C. H NMR (500MHz, CDCl3)
δ 8.37 (d, 2H), 8.34 (d, 2H), 4.45 (s, 3H, 2-CH3).
3-(1-Methyl-1H-tetrazol-5-yl)pyridine (3k) and 3-(2-methyl-
2H-tetrazol-5-yl) pyridine (4k) [23].
(3k) Yellowish crystal;
1
yield 12%; mp 76–78°C (after sublimation). H NMR (500 MHz,
CDCl3) δ 9.01 (s, 1H), 8.85 (d, 1H), 8.17 (d, 1H), 7.58 (m, 1H),
4.24 (s, 3H, 1-CH3). (4k)Yellowish crystal, yield 76%. mp
124–126°C. 1H NMR (500MHz, CDCl3) δ 9.37 (s, 1H), 8.72
(d, 1H), 8.43 (d, 1H), 7.45 (m, 1H), 4.43 (s, 3H, 2-CH3).
4-(1-Methyl-1H-tetrazol-5-yl)pyridine (3l) and 4-(2-methyl-
2H-tetrazol-5-yl) pyridine (4l) [24]. (3l) White solid; yield 8%;
mp 85–86°C (after sublimation). 1H NMR (500 MHz, CDCl3)
δ 8.90 (d, 2H), 7.73 (d, 2H), 4.26 (s, 3H, 1-CH3). (4l) Yellowish
crystals; yield 75%; mp 115–116°C. 1H NMR (500MHz, CDCl3)
δ 8.79 (d, 2H), 8.08 (d, 2H), 4.45 (s, 3H, 2-CH3).
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet